Record Information |
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Version | 1.0 |
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Creation date | 2015-05-07 19:46:52 UTC |
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Update date | 2019-11-26 03:21:51 UTC |
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Primary ID | FDB030678 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | androst-4-en-3,17-dione |
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Description | Androst-4-en-3,17-dione, also known as androstenedione or delta(4)-androsten-3,17-dione, belongs to androgens and derivatives class of compounds. Those are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androst-4-en-3,17-dione is considered to be a steroid lipid molecule. Androst-4-en-3,17-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Androst-4-en-3,17-dione can be found in a number of food items such as naranjilla, purslane, common cabbage, and oval-leaf huckleberry, which makes androst-4-en-3,17-dione a potential biomarker for the consumption of these food products. Androst-4-en-3,17-dione can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. In humans, androst-4-en-3,17-dione is involved in a couple of metabolic pathways, which include androgen and estrogen metabolism and androstenedione metabolism. Androst-4-en-3,17-dione is also involved in a couple of metabolic disorders, which include 17-beta hydroxysteroid dehydrogenase III deficiency and aromatase deficiency. Moreover, androst-4-en-3,17-dione is found to be associated with rheumatoid arthritis, thyroid cancer , cushing's Syndrome, and schizophrenia. Androst-4-en-3,17-dione is a non-carcinogenic (not listed by IARC) potentially toxic compound. |
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CAS Number | 63-05-8 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Androstene-3,17-dione | ChEBI | 4-ANDROSTENE-3-17-dione | ChEBI | delta(4)-Androsten-3,17-dione | ChEBI | delta(4)-Androstene-3,17-dione | ChEBI | Δ(4)-Androsten-3,17-dione | Generator | Δ(4)-Androstene-3,17-dione | Generator | (4)-Androsten-3,17-dione | HMDB | 17-Ketotestosterone | HMDB | 3,17-Dioxoandrost-4-ene | HMDB | 4-Androsten-3,17-dione | HMDB | 4-Androstenedione | HMDB | Androst-4-ene-3,17-dione | HMDB, KEGG | Androstendione | HMDB | D4-Androstene-3,17-dione | HMDB | delta4-Androstenedione | HMDB | Fecundin | HMDB | delta 4 Androstenedione | MeSH, HMDB | delta-4-Androstenedione | MeSH, HMDB | 4 Androstene 3,17 dione | MeSH, HMDB | Androstenedione | HMDB | delta4-Androstene-3,17-dione | HMDB | Δ4-Androstene-3,17-dione | HMDB |
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Predicted Properties | |
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Chemical Formula | C19H26O2 |
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IUPAC name | (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione |
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InChI Identifier | InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1 |
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InChI Key | AEMFNILZOJDQLW-QAGGRKNESA-N |
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Isomeric SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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Average Molecular Weight | 286.4085 |
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Monoisotopic Molecular Weight | 286.193280076 |
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Classification |
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Description | belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- Oxosteroid
- 17-oxosteroid
- 3-oxosteroid
- 3-oxo-delta-4-steroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004l-5910000000-518e1ad38bcc73325b53 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004l-5910000000-5172e05f9889ee2bfaf4 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000f-8940000000-f2892fe3b281d44164c8 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-007d-1960000000-167f1765b095da9d603b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004l-5910000000-518e1ad38bcc73325b53 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004l-5910000000-5172e05f9889ee2bfaf4 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-0590000000-502d6b821317a01a1990 | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0090000000-36e848ba16b141eef47b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-052b-9600000000-712954fc35a84c8217de | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-052b-9300000000-f8e9aa16b4b208b69f7b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-000f-8940000000-e12025ea2b7808c64b9c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-052b-6910000000-b616785c86a92f46158e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-052b-9800000000-73e545a1eb2232d55371 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00kb-5790000000-735473bc44dd70e29259 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00kb-5790000000-114675a4457063901f2b | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0190000000-0347db9e9578e8d5d6f2 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05pc-0490000000-d4049441f1c172450dc3 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uk9-4790000000-355bc0834a6465ecad30 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-887b6f223b77c683ef99 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-9dafdd780cca012f1fb3 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05mo-2190000000-264074b1eefeed0e3103 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-059m-3940000000-9cb32ac21e46afb2829a | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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